Dimethylformamide → HCID 22034366, compound

HRID 1792164Notes

Reaction equation

HRID 1792164 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[C:17]2[C:12](=[CH:13][C:14]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:15][CH:16]=2)[NH:11][C:10]=1[CH2:22]O.CCN(CC)CC.[CH3:31][S:32](Cl)(=[O:34])=[O:33].CN(C=O)C>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[C:17]2[C:12](=[CH:13][C:14]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:15][CH:16]=2)[NH:11][C:10]=1[CH2:22][S:32]([CH3:31])(=[O:34])=[O:33]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22034387HCID 22034387, compound

Product 1

HCID 22034366HCID 22034366, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[3-(2-chloro-phenylsulfanyl)-6-methanesulfonyl-1H-indol-2-yl]-methanol (1 mmole) (as prepared in Example 5) was dissolved in 2 mL CH2Cl2 and treated with 0.3 mL NEt3 followed by 0.08 ml MsCl. After stirring 10 min. 3 mL DMF was added followed by 0.5 g NaSO2Me. The mixture was stirred overnight. The reaction mixture was evaporated to dryness and applied to a PTLC plate. Elution with 1:1 EtOAc/hexane gave 80 mg 3-(2-chloro-phenylsulfanyl)-6-methanesulfonyl-2-methanesulfonylmethyl-1H-indole 601, MS: 343 ([M+H]+).

Workup

  1. stirringThe mixture was stirred overnight
  2. customThe reaction mixture was evaporated to dryness
  3. washElution with 1:1 EtOAc/hexane

Sources & evidence

ORD record
ord-30fdb0db690a400e91fadac5b22e9af3
Source dataset
uspto-grants-2006_07
Patent number
US07074939B2

Reaction notes

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